US8084501B2 - Stable prostaglandin-containing compositions - Google Patents

Stable prostaglandin-containing compositions Download PDF

Info

Publication number: US8084501B2
Authority: US; United States
Prior art keywords: prostaglandin; polysorbate; compositions; travoprost; composition
Prior art date: 2005-01-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Fee Related, expires 2026-07-29

Application number

US11/336,115

Other languages

English (en)

Other versions

US20060270735A1 (en

Inventor

Victor Deaciuc

Michael Hagan

Hashem Heiati

Karen K. Jette

Gary C. Visor

Ian G. C. McAffer

Peter Tasko

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Breath Ltd

Original Assignee

Breath Ltd

Resolution Chemicals Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-01-20

Filing date

2006-01-20

Publication date

2011-12-27

2006-01-20 Application filed by Breath Ltd, Resolution Chemicals Ltd filed Critical Breath Ltd

2006-07-28 Assigned to RESOLUTION CHEMICALS LIMITED reassignment RESOLUTION CHEMICALS LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MCAFFER, IAN G.C., TASKO, PETER

2006-07-28 Assigned to BREATH LIMITED reassignment BREATH LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CARDINAL HEALTH PTS, VISOR, GARY C., DEACIUC, VICTOR, HAGAN, MICHAEL, HEIATI, HASHEM, JETTE, KAREN KOSTICK

2006-07-28 Assigned to BREATH LIMITED reassignment BREATH LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: RESOLUTION CHEMICALS LIMITED

2006-08-18 Assigned to BREATH LIMITED reassignment BREATH LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CARDINAL HEALTH PTS

2006-11-30 Publication of US20060270735A1 publication Critical patent/US20060270735A1/en

2011-11-17 Priority to US13/298,400 priority Critical patent/US20120065258A1/en

2011-12-27 Application granted granted Critical

2011-12-27 Publication of US8084501B2 publication Critical patent/US8084501B2/en

Status Expired - Fee Related legal-status Critical Current

2026-07-29 Adjusted expiration legal-status Critical

Links

0 *[C@H]1C[C@@H](*)[C@H](ccC(=[Y])CCC2=CC([7*])=CC=C2)[C@H]1CccCCCC([1*])([2*])[3*] Chemical compound *[C@H]1C[C@@H](*)[C@H](ccC(=[Y])CCC2=CC([7*])=CC=C2)[C@H]1CccCCCC([1*])([2*])[3*] 0.000 description 1
UCQMLXPCCCRNLA-MQXXSXJYSA-N CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)COC1=CC(C(F)(F)F)=CC=C1.CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1.CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 Chemical compound CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)COC1=CC(C(F)(F)F)=CC=C1.CC(C)OC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1.CCNC(=O)CCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 UCQMLXPCCCRNLA-MQXXSXJYSA-N 0.000 description 1
CTOGGPHHUDWXIF-JBDGNAIASA-N CC1=CC=CC(OC[C@H](O)/C=C/[C@H]2[C@H](O)C[C@H](O)[C@@H]2C/C=C\CCCC(=O)OC(C)C)=C1.CCCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1.CCCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 Chemical compound CC1=CC=CC(OC[C@H](O)/C=C/[C@H]2[C@H](O)C[C@H](O)[C@@H]2C/C=C\CCCC(=O)OC(C)C)=C1.CCCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1.CCCC/C=C\C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1CC[C@@H](O)CCC1=CC=CC=C1 CTOGGPHHUDWXIF-JBDGNAIASA-N 0.000 description 1
WGJJROVFWIXTPA-OALUTQOASA-N CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(=O)O Chemical compound CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(=O)O WGJJROVFWIXTPA-OALUTQOASA-N 0.000 description 1
OEJXZBNIAWQNNI-YNPPLXCJSA-N [H]CCCO[C@@H]1COC(OCCC[H])(OCCCC)[C@@H]1OCCC[H] Chemical compound [H]CCCO[C@@H]1COC(OCCC[H])(OCCCC)[C@@H]1OCCC[H] OEJXZBNIAWQNNI-YNPPLXCJSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/557—Eicosanoids, e.g. leukotrienes or prostaglandins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0048—Eye, e.g. artificial tears
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics

Definitions

compositions according to the invention are preferably formulated so as to be suitable for topical applications, such as in the form of an ophthalmic solution.
Such compositions are preferably suitable for use in the treatment of ophthalmic conditions, such as glaucoma and/or ocular hypertension.
compositions comprising a prostaglandin of the formula (I), as defined in any of the above embodiments. Accordingly, most preferably in the method of the invention the prostaglandin is travoprost of formula (II) above.
compositions (F1 to F6) were then incubated at a range of constant temperatures of 5° C., 25° C., 40° C., 55° C. and 75° C., and assayed for activity/potency and proportion of impurities, at time points of 0, 1, 3, 7, 14 and 21 days (see Tables 2 and 3).
composition containing polysorbate 80 as the surfactant and stabiliser (F2) is less susceptible to chemical degradation at 55° C. and 75° C. than the commercially available preparation, which contains a polyethoxylated castor oil (i.e. chremophor) as the surfactant and stabiliser (F6).
the commercially available composition that had been spiked with 0.4% w/v ethanol (F5) also appears to be more chemically stable than the commercial preparation (F6).

Landscapes

Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Epidemiology (AREA)
Ophthalmology & Optometry (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Bioinformatics & Cheminformatics (AREA)
Organic Chemistry (AREA)
Emergency Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)

US11/336,115 2005-01-20 2006-01-20 Stable prostaglandin-containing compositions Expired - Fee Related US8084501B2 (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
US13/298,400 US20120065258A1 (en)	2005-01-20	2011-11-17	Stable prostaglandin-containing compositions

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB0501192.9A GB0501192D0 (en)	2005-01-20	2005-01-20	Stable prostaglandin-containing compositions
GB0501192.9		2005-01-20

Related Child Applications (1)

Application Number	Title	Priority Date	Filing Date
US13/298,400 Continuation US20120065258A1 (en)	2005-01-20	2011-11-17	Stable prostaglandin-containing compositions

Publications (2)

Publication Number	Publication Date
US20060270735A1 US20060270735A1 (en)	2006-11-30
US8084501B2 true US8084501B2 (en)	2011-12-27

Family

ID=34259405

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
US11/336,115 Expired - Fee Related US8084501B2 (en)	2005-01-20	2006-01-20	Stable prostaglandin-containing compositions
US13/298,400 Abandoned US20120065258A1 (en)	2005-01-20	2011-11-17	Stable prostaglandin-containing compositions

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
US13/298,400 Abandoned US20120065258A1 (en)	2005-01-20	2011-11-17	Stable prostaglandin-containing compositions

Country Status (16)

Country	Link
US (2)	US8084501B2 (pt)
EP (1)	EP1843744A2 (pt)
JP (2)	JP2008528490A (pt)
KR (1)	KR20070094793A (pt)
CN (1)	CN101106973A (pt)
AU (1)	AU2006206649B2 (pt)
BR (1)	BRPI0606606A2 (pt)
CA (1)	CA2595237A1 (pt)
CZ (1)	CZ2007555A3 (pt)
GB (1)	GB0501192D0 (pt)
IL (1)	IL184111A0 (pt)
IS (1)	IS8665A (pt)
NO (1)	NO20073699L (pt)
NZ (1)	NZ556117A (pt)
WO (1)	WO2006078659A2 (pt)
ZA (1)	ZA200705428B (pt)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8722735B2 (en)	2008-03-17	2014-05-13	Alcon Research, Ltd.	Pharmaceutical compositions having desirable bioavailability

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
TWI394564B (zh) *	2006-09-21	2013-05-01	Alcon Res Ltd	自行保存型水性藥學組成物
EP2094839B1 (en)	2006-12-08	2020-02-05	University of Rochester	Expansion of hematopoietic stem cells
JP5297815B2 (ja) *	2007-01-26	2013-09-25	株式会社ポーラファルマ	医薬組成物
WO2008096804A1 (ja) *	2007-02-07	2008-08-14	Teika Pharmaceutical Co., Ltd.	ラタノプロスト含有点眼剤
JP2008247828A (ja) *	2007-03-30	2008-10-16	Wakamoto Pharmaceut Co Ltd	ラタノプロストを含有する水性医薬組成物。
EP2227213B1 (en) *	2007-11-30	2012-08-29	Toltec Pharmaceuticals, Llc	Compositions and methods for treating vaginal infections and pathogenic vaginal biofilms
EP2127638A1 (en) *	2008-05-30	2009-12-02	Santen Pharmaceutical Co., Ltd	Method and composition for treating ocular hypertension and glaucoma
EP2328574A1 (en) *	2008-08-05	2011-06-08	University College Cork-National University of Ireland, Cork	Treatment of retinal degeneration
US20100087540A1 (en) *	2008-10-07	2010-04-08	R-Tech Ueno, Ltd.	Pharmaceutical composition
TW201113022A (en) *	2009-09-01	2011-04-16	R Tech Ueno Ltd	Composition for ocular local-administration for treating ocular hypertension and glaucoma
EP2498784A2 (en) *	2009-11-09	2012-09-19	Allergan, Inc.	Compositions for enhancing hair growth
TWI478730B (zh) *	2009-12-03	2015-04-01	Alcon Res Ltd	眼科乳劑
KR20140038404A (ko) *	2011-04-12	2014-03-28	가부시키가이샤 아루떼꾸 우에노	수성 안과용 조성물
DE102011108948A1 (de) *	2011-07-29	2013-01-31	Achim Göpferich	Wässrige, kolloidale Lösungen von lipophilen Substanzen,insbesondere Arzneistofflösungen
CN104208015A (zh) *	2013-05-29	2014-12-17	天津金耀集团有限公司	含有曲伏前列腺素和防腐剂的眼部制剂
PL3103439T3 (pl) *	2015-06-09	2019-12-31	Medproject Pharma-Entwicklungs- Und Vertriebsgesellschaft Mbh	Zdolny do tworzenia kropli oftalmiczny żel bimatoprostu
EP3643297A4 (en) *	2017-06-22	2021-03-17	Yonsung Fine Chemical Co., Ltd.	OPHTHALMIC COMPOSITION FOR THE TREATMENT OF GLAUCOMA
AU2022267568A1 (en) *	2021-04-30	2023-11-16	Innovent Biologics (Suzhou) Co., Ltd.	Oxm3 storage agent, oxm3 preparation, and preparation method

Citations (27)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1366215A (en)	1916-08-05	1921-01-18	Vaporackumulator Ab	Supplementary power plant for electric centrals
US5165918A (en) *	1988-06-28	1992-11-24	Ciba-Geigy Corporation	Antimicrobial ophthalmic solutions containing dodecyl-dimethyl-(2 phenoxyethyl)-ammonium bromide and methods of using the same
EP0603800A1 (en) *	1992-12-21	1994-06-29	Alcon Laboratories, Inc.	Prostaglandin combinations in glaucoma therapy
WO1995018102A1 (en)	1993-12-28	1995-07-06	Allergan	Cyclopentane(ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents
US5631287A (en)	1994-12-22	1997-05-20	Alcon Laboratories, Inc.	Storage-stable prostaglandin compositions
US5670537A (en)	1992-08-03	1997-09-23	Bristol-Meyers Squibb Company	Method for effecting tumor regression with a low dose, short infusion taxol regimen
WO1998041208A1 (en) *	1997-03-17	1998-09-24	Novartis Ag	Compositions and methods for reducing ocular hypertension
WO1999002164A1 (en)	1997-07-10	1999-01-21	Synphora Ab	Method and composition for treatment of erectile dysfunction
WO1999002165A1 (en)	1997-07-11	1999-01-21	Pharmacia & Upjohn Ab	Prostaglandin derivatives devoid of side-effects for the treatment of glaucoma
WO1999012899A1 (en)	1997-09-09	1999-03-18	The Procter & Gamble Company	A process for making prostaglandin f analogs
US5889052A (en)	1993-08-03	1999-03-30	Alcon Laboraties, Inc.	Use of cloprostenol and fluprostenol analogues to treat glaucoma and ocular hypertension
US5972991A (en)	1992-09-21	1999-10-26	Allergan	Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
US6011062A (en)	1994-12-22	2000-01-04	Alcon Laboratories, Inc.	Storage-stable prostaglandin compositions
WO2000020386A1 (en)	1998-10-05	2000-04-13	Alcon Laboratories, Inc.	Stannane synthesis of prostanoids
WO2000040248A1 (en)	1999-01-08	2000-07-13	Synphora Ab	Method and composition for treatment of female sexual dysfunction
US6235781B1 (en)	1998-07-14	2001-05-22	Alcon Laboratories, Inc.	Prostaglandin product
US6319943B1 (en)	1999-10-25	2001-11-20	Supergen, Inc	Oral formulation for paclitaxel
WO2002038158A1 (en)	2000-11-13	2002-05-16	Pharmacia Ab	Improved treatment
US6417228B1 (en)	1998-11-02	2002-07-09	Alcon Manufacturing, Ltd..	13-Aza prostaglandins for the treatment of glaucoma and ocular hypertension
US20020103255A1 (en)	1997-12-19	2002-08-01	Hellberg Mark R.	Use of non-steroidal anti-inflammatory agents in combination with prostaglandin FP receptor agonists to treat glaucoma and ocular hypertension
EP1321144A1 (en)	2000-09-13	2003-06-25	Santen Pharmaceutical Co., Ltd.	Eye drops
US20030147823A1 (en)	2002-02-04	2003-08-07	Allergan, Inc.	Method of enhancing hair growth
US20040023954A1 (en) *	2002-08-05	2004-02-05	Ling Kah-Hiing John	9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma
WO2004022063A1 (ja)	2002-09-09	2004-03-18	Santen Pharmaceutical Co., Ltd.	ラタノプロストを有効成分とする澄明な点眼液
US20040076678A1 (en)	2002-08-21	2004-04-22	Sucampo Ag	Opthalmic solution
US20040082660A1 (en)	2002-10-24	2004-04-29	Ryuji Ueno	Method for treating ocular hypertension and glaucoma
US6743439B1 (en) *	2001-06-27	2004-06-01	Alcon, Inc.	Ophthalmic compositions containing copolymers of sulfonated styrene and maleic anhydride

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0458588B1 (en) *	1990-05-22	1994-11-30	R-Tech Ueno Ltd.	Treatment of ocular hypertension with a synergistic combination for ocular administration
AU7680096A (en) *	1995-12-22	1997-07-17	Alcon Laboratories, Inc.	Combinations of dp and fp type prostaglandins for lowering iop
JP3876355B2 (ja) *	2000-09-13	2007-01-31	参天製薬株式会社	点眼液
NO317079B1 (no) *	2002-08-02	2004-08-02	Maritime Hydraulics As	Stigerorstrekkanordning

2005
- 2005-01-20 GB GBGB0501192.9A patent/GB0501192D0/en not_active Ceased
2006
- 2006-01-18 NZ NZ556117A patent/NZ556117A/en not_active IP Right Cessation
- 2006-01-18 BR BRPI0606606-2A patent/BRPI0606606A2/pt not_active IP Right Cessation
- 2006-01-18 CA CA002595237A patent/CA2595237A1/en not_active Abandoned
- 2006-01-18 KR KR1020077016516A patent/KR20070094793A/ko not_active Withdrawn
- 2006-01-18 EP EP06718670A patent/EP1843744A2/en not_active Withdrawn
- 2006-01-18 WO PCT/US2006/001626 patent/WO2006078659A2/en not_active Ceased
- 2006-01-18 JP JP2007552216A patent/JP2008528490A/ja active Pending
- 2006-01-18 AU AU2006206649A patent/AU2006206649B2/en not_active Ceased
- 2006-01-18 CN CNA2006800023897A patent/CN101106973A/zh active Pending
- 2006-01-20 US US11/336,115 patent/US8084501B2/en not_active Expired - Fee Related
2007
- 2007-06-21 IL IL184111A patent/IL184111A0/en unknown
- 2007-07-03 ZA ZA200705428A patent/ZA200705428B/xx unknown
- 2007-07-17 NO NO20073699A patent/NO20073699L/no not_active Application Discontinuation
- 2007-08-02 IS IS8665A patent/IS8665A/is unknown
- 2007-08-16 CZ CZ20070555A patent/CZ2007555A3/cs unknown
2011
- 2011-11-17 US US13/298,400 patent/US20120065258A1/en not_active Abandoned
2012
- 2012-12-27 JP JP2012286362A patent/JP2013056948A/ja active Pending

Patent Citations (30)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US1366215A (en)	1916-08-05	1921-01-18	Vaporackumulator Ab	Supplementary power plant for electric centrals
US5165918A (en) *	1988-06-28	1992-11-24	Ciba-Geigy Corporation	Antimicrobial ophthalmic solutions containing dodecyl-dimethyl-(2 phenoxyethyl)-ammonium bromide and methods of using the same
US5670537A (en)	1992-08-03	1997-09-23	Bristol-Meyers Squibb Company	Method for effecting tumor regression with a low dose, short infusion taxol regimen
US5972991A (en)	1992-09-21	1999-10-26	Allergan	Cyclopentane heptan(ene) oic acid, 2-heteroarylalkenyl derivatives as therapeutic agents
EP0603800A1 (en) *	1992-12-21	1994-06-29	Alcon Laboratories, Inc.	Prostaglandin combinations in glaucoma therapy
US5889052A (en)	1993-08-03	1999-03-30	Alcon Laboraties, Inc.	Use of cloprostenol and fluprostenol analogues to treat glaucoma and ocular hypertension
AU704670B2 (en)	1993-08-03	1999-04-29	Alcon Laboratories, Inc.	Use of cloprostenol, fluprostenol and their analogues to treat glaucoma and ocular hypertension
WO1995018102A1 (en)	1993-12-28	1995-07-06	Allergan	Cyclopentane(ene) heptenoic or heptanoic acids and derivatives thereof useful as therapeutic agents
US6011062A (en)	1994-12-22	2000-01-04	Alcon Laboratories, Inc.	Storage-stable prostaglandin compositions
US5849792A (en)	1994-12-22	1998-12-15	Alcon Laboratories, Inc.	Storage-stable prostaglandin compositions
US5631287A (en)	1994-12-22	1997-05-20	Alcon Laboratories, Inc.	Storage-stable prostaglandin compositions
WO1998041208A1 (en) *	1997-03-17	1998-09-24	Novartis Ag	Compositions and methods for reducing ocular hypertension
WO1999002164A1 (en)	1997-07-10	1999-01-21	Synphora Ab	Method and composition for treatment of erectile dysfunction
WO1999002165A1 (en)	1997-07-11	1999-01-21	Pharmacia & Upjohn Ab	Prostaglandin derivatives devoid of side-effects for the treatment of glaucoma
WO1999012899A1 (en)	1997-09-09	1999-03-18	The Procter & Gamble Company	A process for making prostaglandin f analogs
US20020103255A1 (en)	1997-12-19	2002-08-01	Hellberg Mark R.	Use of non-steroidal anti-inflammatory agents in combination with prostaglandin FP receptor agonists to treat glaucoma and ocular hypertension
US6235781B1 (en)	1998-07-14	2001-05-22	Alcon Laboratories, Inc.	Prostaglandin product
WO2000020386A1 (en)	1998-10-05	2000-04-13	Alcon Laboratories, Inc.	Stannane synthesis of prostanoids
US6417228B1 (en)	1998-11-02	2002-07-09	Alcon Manufacturing, Ltd..	13-Aza prostaglandins for the treatment of glaucoma and ocular hypertension
WO2000040248A1 (en)	1999-01-08	2000-07-13	Synphora Ab	Method and composition for treatment of female sexual dysfunction
US6319943B1 (en)	1999-10-25	2001-11-20	Supergen, Inc	Oral formulation for paclitaxel
US20040097592A1 (en)	2000-09-13	2004-05-20	Kenji Morishima	Eye drops
EP1321144A1 (en)	2000-09-13	2003-06-25	Santen Pharmaceutical Co., Ltd.	Eye drops
WO2002038158A1 (en)	2000-11-13	2002-05-16	Pharmacia Ab	Improved treatment
US6743439B1 (en) *	2001-06-27	2004-06-01	Alcon, Inc.	Ophthalmic compositions containing copolymers of sulfonated styrene and maleic anhydride
US20030147823A1 (en)	2002-02-04	2003-08-07	Allergan, Inc.	Method of enhancing hair growth
US20040023954A1 (en) *	2002-08-05	2004-02-05	Ling Kah-Hiing John	9,11-cycloendoperoxide pro-drugs of prostaglandin analogues for treatment of ocular hypertension and glaucoma
US20040076678A1 (en)	2002-08-21	2004-04-22	Sucampo Ag	Opthalmic solution
WO2004022063A1 (ja)	2002-09-09	2004-03-18	Santen Pharmaceutical Co., Ltd.	ラタノプロストを有効成分とする澄明な点眼液
US20040082660A1 (en)	2002-10-24	2004-04-29	Ryuji Ueno	Method for treating ocular hypertension and glaucoma

Non-Patent Citations (19)

* Cited by examiner, † Cited by third party
Title
Alexander et al., Annals of Pharmacotherpay, 36(3), p. 504-511, 2002. *
BASF Technical Leaflet, "Cremophor EL", pp:1-7, Jul. 1997.
Ciucanu et al., "Derivatizations of prostaglandins and related compounds to (methoxime) alkyl ester alkyl ether derivatives for gas chromatographic analysis," Chemical Abstracts, 109:664 (1988).
European Search Report for corresponding Application No. 06178670.0, dated Mar. 18, 2008.
Ikegami et al., "9,15-Bis(arylsilyl)prostaglandin F2alpha derivatives," Chemical Abstracts, 105:650 (1986).
Ikegami et al., "9,15-Bis(arylsilyl)prostaglandin F2α derivatives," Chemical Abstracts, 105:650 (1986).
International Preliminary Report on Patentability for corresponding International Application No. PCT/US2006/001626, dated Jul. 24, 2007.
International Search Report for corresponding International Application No. PCT/US2006/001626, dated Jul. 25, 2006.
Kerstetter el al., "Prostaglandin F2 Alpha-1-Isopropylester Lowers Intraocular Pressure Without Decreasing Aqueous Humor Flow", J. Ophthalmol, 105:30-34 (1988). (abstract).
Lijebris et al., "Ligand-controlled palladium-catalyzed intramolecular reactions of phenyl-substituted prostaglandin F2alpha analogues," Tetrahedron, 51:9139-9154 (1995).
Lijebris et al., "Ligand-controlled palladium-catalyzed intramolecular reactions of phenyl-substituted prostaglandin F2α analogues," Tetrahedron, 51:9139-9154 (1995).
Miyazaki et al., "Dimethylisopropylsilyl ether derivatives in gas chromatography mass spectrometry fo prostaglandins and thromboxane B2," Chemical Abstracts, 96:90-91 (1982).
Morozowich et al., "Prostaglandin prodrugs. II: New method for synthesizing prostaglandin C1-aliphatic esters," Chemical Abstracts, 91:603 (1979).
Oda et al., Cell Injury Effect of Isopropyl Unoprostone, an Antiglaucoma Agent, on Cultured Human Conjunctival Cells, J. Ocul Pharmacol Ther., 15:489-496 (1999). (abstract).
Product page for Sigma T6687 from www.sigmaldrich.com, accessed Dec. 4, 2007. *
Tabassi et al., The Effects of Polysorbate Surfactants on the Structure of Mucus Glycoproteins, http://diglib.tums.ac.ir/U.j/daru/vol9n12/sajjadi.htm, pp:1-10 (2004).
United Kingdom Intellectual Property Office Search Report for corresponding Application No. GB0501192.9, dated Apr. 19, 2005.
Waddell et al., "Combined capillary column gas chromatography negative ion chemical ionization mass spectrometry of prostanoids," Chemical Abstracts, 99:87498 (1983).
Written Opinion of the International Searching Authority for corresponding International Application No. PCT/US2006/001626, dated Jul. 25, 2006.

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